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5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → N-(2-Amino-ethyl)-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonamide

HRID 1685761
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인쇄 미리보기

반응식

HRID 1685761 반응식
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:23])[NH:21][OH:22])=[CH:16][CH:15]=1)(=[O:13])=[O:12])(C)(C)C.[CH2:25]([N:27]([CH2:30][C:31]1[S:35][C:34]([C:36](O)=O)=[CH:33][C:32]=1[CH3:39])[CH2:28][CH3:29])[CH3:26]>Cl.O1CCOCC1.O>[NH2:7][CH2:8][CH2:9][NH:10][S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:23]=[C:36]([C:34]3[S:35][C:31]([CH2:30][N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[C:32]([CH3:39])[CH:33]=3)[O:22][N:21]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:13]
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참가 물질

6

반응물 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178453718HCID 178453718, 화합물

생성물 1

HCID 67265224N-(2-Amino-ethyl)-4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonamide수율 3.5%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매
HCID 31275
1,4-Dioxane
용매

실험 절차

Crude (2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-ethyl)-carbamic acid tert-butyl ester (156 mg) is obtained starting from {2-[4-(N-hydroxycarbamimidoyl)-benzenesulfonylamino]-ethyl}-carbamic acid tert-butyl ester (277 mg, 0.774 mmol) and 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (160 mg, 0.704 mmol) according to Method A; LC-MS: tR=0.61 min; [M+1]+=550.16. This material (156 mg, 0.284 mmol) is dissolved in 4 M HCl in dioxane (5 mL) and the mixture is stirred at rt for 18 h. The mixture is diluted with water and washed with EA. The organic washing is extracted with water. The combined aq. extracts are neutralised by adding sat. aq. NaHCO3 solution and extracted twice with EA. These organic extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC (XBridge, eluting with a gradient of acetonitrile in water containing 0.5% of aq. ammonia) to give the title compound (11 mg) as a pale yellow oil; LC-MS: tR=0.42 min; [M+1]+=449.64.

후처리

  1. washwashed with EA
  2. washThe organic washing
  3. extractionis extracted with water
  4. additionby adding sat. aq. NaHCO3 solution
  5. extractionextracted twice with EA
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by prep
  10. washHPLC (XBridge, eluting with a gradient of acetonitrile in water containing 0.5% of aq. ammonia)

출처 및 근거

ORD 기록
ord-a07fc819e92c4c53a76a5f4d39f85074
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08148410B2

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